Me and My Best Friend on our Family Vacation

by Jackson123

5 Jul 2020 6530 readers Score 9.3 (104 votes) PDF Mobi ePub Txt


I slowly shut the door as to not wake anyone and made my way downstairs. The house that my parents and their friends had rented for our vacation to Croatia was massive, with multiple floors, great views, and perhaps my favorite part, a basement complete with a home spa. The trip was fun and all, especially since I had one of my best friends Dylan there;however, too much family time forced me to use up my late nights to unwind in the basement. I made a stop in the kitchen to grab a bottle of wine from my parents stash and made my way down the cold stone stairs and into the basement. In the locker room, I stripped down to my bare body and shivered. Across the room was a full-length mirror, where I caught myself checking out my body.I had just turned 16 and puberty seemed to be dealing my cards nicely: I had a pretty chiseled figure measuring about 6’2”, with veins running down my body from my neck all the way to my huge dick. I had never really thought I owned a large cock until we started showering after basketball practice (out of all of my teammates, my 9” hard uncut dick out measured them all.)


“Enough, Jackson,” I scolded myself. I grabbed the bottle of wine and after taking a couple swigs, walked into the spa jerking myself off a little bit (alcohol always makes me horny.) To my surprise, Dylan was already in the hot tub facing the other way, and from what I could tell, totally butt naked too. Apart from me, Dylan was one of the hottest guys at our school, with green eyes, jet black curly hair, and an extremely sharp jawline. Everyone knew he was gorgeous, and I was no exception. I had just accepted that I was bisexual and Dylan was the center of many of my gay fantasies.

“What are you doing down here? Looks like we had the same idea” I said, jumping in the spot across from him.

“Oh hey Jackson,” he responded. “I just can’t get over this knot in my back. I think it was from our hike today. I thought I would come down here and relax in the hot tub.”

Seeing my chance, I quickly responded, “If you want, I could try to get it out for you. We have a whole spa and I wouldn’t want my beautiful hands to go to waste tonight.”Dylan smiled and after a little bit of convincing, he rose out of the pool, toweled off a little bit and hoisted himself onto the massage table. I reached over and, trying to hold back my boner, lubed up my hands.Dylan’s had a hug bubble butt, complete with an entirely smooth surface.

“Woah!” I retorted as I began to rub down his lower back. “You’ve been shaving down here or something, Dylan?”To my surprise, he began to tell me how during junior year, he used to meet up with guys through chat rooms after he broke up with his girlfriend at the time.

“I was thinking that a blowjob is a blowjob, right? Anyways in the end, I sort of got accustomed to the feeling of getting fucked in the ass, hence the nicely trimmed lawn down there,” he said while I stood there shocked. “I haven’t done that in a while but damn I used to love that feeling.”

Slowly, seeing my chance, I worked my way down from his back and onto his huge muscle of an ass. “You know,” I said.“Anytime you need to release a load you can always call me. You know I swing the other way and I would be happy to help you out.” I got to his hole, which I could tell had seen it’s share of monster cocks. Holding back nothing, I slipped a lubed finger down his ass and began to pump away, adding more fingers as fast as I could ease them in. He really wasn’t kidding about liking the feeling: his moans became louder and louder as I ventured deeper into his hole.With my other hand I covered his mouth, afraid that his deep moans were going to wake our families up.

He suddenly flipped over, grabbed my neck and began to kiss me, gently at first and then eventually joined my tongue as it danced around our mouths. I could feel his strong, manly hands all over my neck and back, his cold rings digging into my skin. He pulled away, and seeing my dick rock hard and soaked in precum, threw me onto the table.

“Oooohh Dylan!” I moaned, no longer caring about our noise. He was noticeably experienced, his tongue doing things that no girl was ever able to do. “I’m going to cum!” I whispered not long after. Before I could, however, Dylan came back on top of me and started to kiss me again, his lips salty with my fluids.

“Fuck me,” he whispered to me gently, but with the power of a thousand screaming voices. I grabbed the base of my dick, which was throbbing with cum, and rubbed the massage lotion up and down my huge shaft.Dylan, holding and chugging the bottle of wine, got down on all fours and spread his huge cheeks open wide. Slowly and with extreme concentration, I began pushing my hot red cock into his ass, which was already dripping with the delicious juices of his insides. After a couple slow thrusts and a lot of moaning, I began pumping harder and harder, obtaining the rhythmic rocking of a wild animal. I slapped his ass cheeks until they were red; this was better than any other girl I’d fucked before.

I got up, threw him against the hot tub, and bent him over the ledge with his right leg resting on top of it. I continued this savage motion as Dylan’s hard dick swayed back and forth. His screams intensified and so did my strokes, my full bush of dark blonde hair banging against his bare ass.

He continued moaning and begging for more of my huge cock, and I was pushed to the edge. I couldn’t hold it any longer and began to shoot hot ropes of my cum down his asshole. I counted one, two, three, four, five full loads, the most I’ve ever come by far. Dylan turned around and kissed me passionately, jerking himself off until he came all over his chiseled abs.I bent down and eagerly licked all of his warm, salty juice off of his body and we kissed once more, spreading the cum to the depths of our mouths.

“Wow,” was all that Dylan could say between his panting deep breaths, similar to after he finishes a hard game of soccer. “Let’s do that again some time,” he finished as we walked upstairs and climbed into bed, our naked bodies entangled as we drifted off to sleep.